The alkylation of aromatic hydrocarbon compounds employing zeolite catalysts is known and understood in the art. U.S. Pat. No. 5,334,795 describes the liquid phase alkylation of benzene with ethylene in the presence of MCM-22 to produce ethylbenzene; and U.S. Pat. No. 4,891,458 discloses liquid phase alkylation and transalkylation processes using zeolite beta.
Zeolite-based catalysts are used in the alkylation of benzene with propylene to produce cumene. U.S. Pat. No. 4,992,606 discloses a process for preparing cumene using MCM-22 in liquid phase.
U.S. Patent Publication No. 2008/0027259, U.S. Ser. No. 11/823,129, the entire content of which is fully incorporated by reference, discloses a crystalline molecular sieve, in its as-synthesized form, identified as EMM-10-P, a method of making EMM-10-P. In some embodiments of the U.S. Patent Publication No. 2008/0027259, U.S. patent application Ser. No. 11/823,129, the EMM-10-P has, in its as-synthesized form, an X-ray diffraction pattern including d-spacing maxima at 13.18±0.25 and 12.33±0.23 Angstroms, wherein the peak intensity of the d-spacing maximum at 13.18±0.25 Angstroms is at least as great as 90% of the peak intensity of the d-spacing maximum at 12.33±0.23 Angstroms. In addition, the X-ray diffraction pattern of the EMM-10-P may further include two XRD distinguishable peaks with d-spacing maxima at 11.06±0.18 and 9.25±0.13 Angstroms, wherein the peak intensity of the d-spacing maximum at 11.06±0.18 Angstroms is at least as great as the peak intensity of the d-spacing maximum at 9.25±0.13 Angstroms. Additionally, the peaks with d-spacing maxima at 11.06±0.18 and 9.25±0.13 Angstroms may be non-discrete peaks.
U.S. Patent Publication No. 2008/0027256, U.S. Ser. No. 11/824,742, the entire content of which is fully incorporated by reference, disclose novel molecular sieves designated as EMM-10, and the method making the same. In some embodiments of U.S. Patent Publication No. 2008/0027256, U.S. Ser. No. 11/824,742, the EMM-10, in its ammonium exchanged form or in its calcined form, comprises unit cells with MWW topology, the crystalline molecular sieve is characterized by diffraction streaking from the unit cell arrangement in the c direction. In addition, the EMM-10 may further be characterized by the arced hk0 patterns of electron diffraction pattern. In further additional embodiments of the U.S. Ser. No. 11/824,742, the EMM-10 may further be characterized by the unit cells streaking along c direction.
U.S. Patent Publication No. 2008/0045768, U.S. Ser. No. 11/827,953, the entire content of which is fully incorporated by reference, discloses a crystalline MCM-22 family molecular sieve having, in its as-synthesized form, an X-ray diffraction pattern including a peak at d-spacing maximum of 12.33±0.23 Angstroms, a distinguishable peak at a d-spacing maximum between 12.57 to about 14.17 Angstroms and a non-discrete peak at a d-spacing maximum between 8.8 to 11. Angstroms, wherein the peak intensity of the d-spacing maximum between 12.57 to about 14.17 Angstroms is less than 90% of the peak intensity of the d-spacing maximum at 12.33±0.23 Angstroms.
A molecular sieve composition as described or characterized in U.S. Patent Publication Nos. 2008/0027259, 2008/0027256 and/or 2008/0027256, Ser. Nos. 11/823,129, 11/824,742, and/or 11/827,953 is designated as an EMM-10 family molecular sieve as used herein this disclosure.
The alkylation of benzene with ethylene and propylene to form ethylbenzene (EB) and cumene respectively is diffusionally limited. There is, therefore, a need to develop high activity catalyst for the alkylation of benzene with ethylene and propylene. We discovered that a composition comprising a MCM-22 family material, such as a crystalline MCM-49 molecular sieve and/or a crystalline MCM-22 molecular sieve, and titanium compound exhibits high alkylation activity.